# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_audit_block_doi                 10.5517/ccdc.csd.cc22hp2c
_database_code_depnum_ccdc_archive 'CCDC 1921692'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.joc.9b01626 2019
loop_
_audit_author_name
_audit_author_address
'Shun-Yi Wang'
;Soochow University
China
;
_audit_update_record             
;
2019-06-08 deposited with the CCDC.	2019-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 O4 S Se'
_chemical_formula_weight         471.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.4860(10)
_cell_length_b                   15.1787(18)
_cell_length_c                   16.604(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.430(4)
_cell_angle_gamma                90
_cell_volume                     2120.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9789
_cell_measurement_theta_min      2.6838
_cell_measurement_theta_max      27.1997

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.895
_shelx_estimated_absorpt_T_min   0.764
_shelx_estimated_absorpt_T_max   0.833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3552
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker ApexII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            56715
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.768
_diffrn_reflns_theta_max         27.564
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4875
_reflns_number_gt                3940
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0630P)²+1.7153P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4875
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1229
_refine_ls_wR_factor_gt          0.1134
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.60954(3) 0.63857(2) 0.17353(2) 0.05462(13) Uani 1 1 d . . . . .
S1 S 0.23121(9) 0.52343(5) 0.30944(4) 0.04788(18) Uani 1 1 d . . . . .
O1 O 0.2926(3) 0.48413(17) 0.38569(13) 0.0709(7) Uani 1 1 d . . . . .
O2 O 0.1369(3) 0.60150(15) 0.30865(16) 0.0689(7) Uani 1 1 d . . . . .
O3 O 0.5747(3) 0.42329(14) 0.29559(16) 0.0694(7) Uani 1 1 d . . . . .
O4 O 0.6391(2) 0.55498(13) 0.35104(12) 0.0506(5) Uani 1 1 d . . . . .
C1 C 0.5481(4) 0.49997(18) 0.30427(16) 0.0447(6) Uani 1 1 d . . . . .
C2 C 0.4037(3) 0.54622(16) 0.26231(15) 0.0390(5) Uani 1 1 d . . . . .
C3 C 0.4057(3) 0.60203(16) 0.20031(15) 0.0365(5) Uani 1 1 d . . . . .
C4 C 0.2631(3) 0.63973(16) 0.15136(15) 0.0377(5) Uani 1 1 d . . . . .
C5 C 0.2191(4) 0.7265(2) 0.1614(2) 0.0537(7) Uani 1 1 d . . . . .
H5 H 0.280304 0.762580 0.198398 0.064 Uiso 1 1 calc R U . . .
C6 C 0.0840(4) 0.7590(2) 0.1163(2) 0.0662(9) Uani 1 1 d . . . . .
H6 H 0.053030 0.816879 0.123768 0.079 Uiso 1 1 calc R U . . .
C7 C -0.0059(4) 0.7064(3) 0.0600(2) 0.0689(10) Uani 1 1 d . . . . .
H7 H -0.097280 0.728652 0.029874 0.083 Uiso 1 1 calc R U . . .
C8 C 0.0400(4) 0.6220(3) 0.0489(2) 0.0686(10) Uani 1 1 d . . . . .
H8 H -0.019501 0.586838 0.010432 0.082 Uiso 1 1 calc R U . . .
C9 C 0.1751(4) 0.5878(2) 0.09436(18) 0.0515(7) Uani 1 1 d . . . . .
H9 H 0.205792 0.530009 0.086317 0.062 Uiso 1 1 calc R U . . .
C10 C 0.1206(3) 0.44320(18) 0.24956(17) 0.0463(6) Uani 1 1 d . . . . .
C11 C 0.1816(4) 0.3592(2) 0.2457(2) 0.0596(8) Uani 1 1 d . . . . .
H11 H 0.281370 0.345444 0.272845 0.071 Uiso 1 1 calc R U . . .
C12 C 0.0921(5) 0.2960(3) 0.2011(3) 0.0743(10) Uani 1 1 d . . . . .
H12 H 0.132238 0.239322 0.197784 0.089 Uiso 1 1 calc R U . . .
C13 C -0.0548(5) 0.3160(3) 0.1616(2) 0.0751(10) Uani 1 1 d . . . . .
H13 H -0.115050 0.272783 0.132169 0.090 Uiso 1 1 calc R U . . .
C14 C -0.1133(5) 0.4001(3) 0.1654(3) 0.0792(11) Uani 1 1 d . . . . .
H14 H -0.212830 0.413655 0.137969 0.095 Uiso 1 1 calc R U . . .
C15 C -0.0262(4) 0.4645(2) 0.2095(2) 0.0641(9) Uani 1 1 d . . . . .
H15 H -0.066165 0.521311 0.212140 0.077 Uiso 1 1 calc R U . . .
C16 C 0.5552(3) 0.67541(19) 0.06276(17) 0.0443(6) Uani 1 1 d . . . . .
C17 C 0.5080(4) 0.7607(2) 0.0460(2) 0.0583(8) Uani 1 1 d . . . . .
H17 H 0.496630 0.800014 0.087881 0.070 Uiso 1 1 calc R U . . .
C18 C 0.4775(5) 0.7874(3) -0.0347(3) 0.0800(12) Uani 1 1 d . . . . .
H18 H 0.444350 0.844787 -0.046924 0.096 Uiso 1 1 calc R U . . .
C19 C 0.4958(6) 0.7303(4) -0.0954(3) 0.0907(14) Uani 1 1 d . . . . .
H19 H 0.475130 0.748935 -0.149132 0.109 Uiso 1 1 calc R U . . .
C20 C 0.5442(5) 0.6458(3) -0.0787(3) 0.0834(13) Uani 1 1 d . . . . .
H20 H 0.556686 0.607264 -0.120969 0.100 Uiso 1 1 calc R U . . .
C21 C 0.5748(4) 0.6173(2) 0.0007(2) 0.0614(8) Uani 1 1 d . . . . .
H21 H 0.608202 0.559796 0.012367 0.074 Uiso 1 1 calc R U . . .
C23 C 0.7778(4) 0.5177(2) 0.4009(2) 0.0643(9) Uani 1 1 d . . . . .
H23A H 0.847418 0.489574 0.366633 0.077 Uiso 1 1 calc R U . . .
H23B H 0.744692 0.473871 0.437783 0.077 Uiso 1 1 calc R U . . .
C24 C 0.8614(4) 0.5906(3) 0.4470(2) 0.0688(9) Uani 1 1 d . . . . .
H24A H 0.895042 0.632987 0.409855 0.103 Uiso 1 1 calc R U . . .
H24B H 0.952541 0.567908 0.480929 0.103 Uiso 1 1 calc R U . . .
H24C H 0.791043 0.618247 0.480150 0.103 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C16 1.921(3) . ?
Se1 C3 1.923(2) . ?
S1 O2 1.429(2) . ?
S1 O1 1.435(2) . ?
S1 C10 1.764(3) . ?
S1 C2 1.781(3) . ?
O3 C1 1.198(3) . ?
O4 C1 1.320(3) . ?
O4 C23 1.462(4) . ?
C1 C2 1.503(4) . ?
C2 C3 1.335(4) . ?
C3 C4 1.482(4) . ?
C4 C9 1.376(4) . ?
C4 C5 1.385(4) . ?
C5 C6 1.377(5) . ?
C6 C7 1.381(5) . ?
C7 C8 1.358(5) . ?
C8 C9 1.389(5) . ?
C10 C15 1.372(4) . ?
C10 C11 1.381(4) . ?
C11 C12 1.378(5) . ?
C12 C13 1.365(6) . ?
C13 C14 1.374(6) . ?
C14 C15 1.378(6) . ?
C16 C17 1.373(4) . ?
C16 C21 1.382(5) . ?
C17 C18 1.391(5) . ?
C18 C19 1.354(7) . ?
C19 C20 1.365(7) . ?
C20 C21 1.381(6) . ?
C23 C24 1.474(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 Se1 C3 101.16(11) . . ?
O2 S1 O1 119.46(16) . . ?
O2 S1 C10 108.10(15) . . ?
O1 S1 C10 108.44(14) . . ?
O2 S1 C2 109.04(13) . . ?
O1 S1 C2 104.07(14) . . ?
C10 S1 C2 107.11(12) . . ?
C1 O4 C23 117.0(2) . . ?
O3 C1 O4 125.5(3) . . ?
O3 C1 C2 123.6(3) . . ?
O4 C1 C2 110.9(2) . . ?
C3 C2 C1 124.3(2) . . ?
C3 C2 S1 123.7(2) . . ?
C1 C2 S1 111.89(18) . . ?
C2 C3 C4 125.2(2) . . ?
C2 C3 Se1 117.57(19) . . ?
C4 C3 Se1 117.17(17) . . ?
C9 C4 C5 119.8(3) . . ?
C9 C4 C3 119.2(2) . . ?
C5 C4 C3 121.0(2) . . ?
C6 C5 C4 119.6(3) . . ?
C5 C6 C7 120.6(3) . . ?
C8 C7 C6 119.6(3) . . ?
C7 C8 C9 120.7(3) . . ?
C4 C9 C8 119.8(3) . . ?
C15 C10 C11 121.1(3) . . ?
C15 C10 S1 119.6(2) . . ?
C11 C10 S1 119.2(2) . . ?
C12 C11 C10 118.9(3) . . ?
C13 C12 C11 120.6(4) . . ?
C12 C13 C14 119.7(4) . . ?
C13 C14 C15 120.8(4) . . ?
C10 C15 C14 118.8(3) . . ?
C17 C16 C21 120.7(3) . . ?
C17 C16 Se1 119.7(2) . . ?
C21 C16 Se1 119.4(2) . . ?
C16 C17 C18 118.8(4) . . ?
C19 C18 C17 120.5(4) . . ?
C18 C19 C20 120.7(4) . . ?
C19 C20 C21 120.2(4) . . ?
C20 C21 C16 119.1(4) . . ?
O4 C23 C24 107.5(3) . . ?

_refine_diff_density_max         1.545
_refine_diff_density_min         -1.218
_refine_diff_density_rms         0.069

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_785
_database_code_depnum_ccdc_archive 'CCDC 1921697'
loop_
_audit_author_name
_audit_author_address
'Shihao Chen'
;East Normal China University
China
;
_audit_update_record             
;
2019-06-08 deposited with the CCDC.	2019-12-05 downloaded from the CCDC.
;
_audit_creation_date             2019-04-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H10 O2 S'
_chemical_formula_sum            'C11 H10 O2 S'
_chemical_formula_weight         206.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.23740(10)
_cell_length_b                   10.35780(10)
_cell_length_c                   16.95870(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1973.90(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    22811
_cell_measurement_temperature    292.7(6)
_cell_measurement_theta_max      74.1800
_cell_measurement_theta_min      4.7960
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.664
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            45068
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.393
_diffrn_reflns_theta_min         5.216
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.7(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  13.00   1.00    1.00    --    0.00  38.00 -60.00   32
  2  ω    -43.00  24.00   1.00    1.00    --    0.00 -77.00 -30.00   67
  3  ω     55.00  81.00   1.00    1.00    --    0.00  57.00-150.00   26
  4  ω    -22.00  42.00   1.00    1.00    --    0.00  57.00  60.00   64
  5  ω    -26.00  19.00   1.00    1.00    --    0.00 -38.00-150.00   45
  6  ω    -23.00  89.00   1.00    1.00    --    0.00  57.00 150.00  112
  7  ω    -82.00 -57.00   1.00    1.00    --    0.00 -77.00 -30.00   25
  8  ω    -87.00 -44.00   1.00    1.00    --    0.00 -38.00-150.00   43
  9  ω     35.00  61.00   1.00    1.00    --    0.00  38.00 -60.00   26
 10  ω     45.00  89.00   1.00    1.00    --    0.00  57.00  60.00   44
 11  ω    -20.00  21.00   1.00    1.00    --    0.00  57.00-150.00   41
 12  ω    -19.00  87.00   1.00    1.00    --    0.00  38.00 -30.00  106
 13  ω    120.00 182.00   1.00    1.00    --   95.80  77.00-128.97   62
 14  ω     65.00  95.00   1.00    1.00    --   95.80  77.00-128.97   30
 15  ω    149.00 175.00   1.00    1.00    --   95.80  64.00 -48.67   26
 16  ω    145.00 182.00   1.00    1.00    --   95.80  63.00 124.08   37
 17  ω     70.00  99.00   1.00    1.00    --   95.80  63.00 124.08   29
 18  ω     70.00 111.00   1.00    1.00    --   95.80  64.00 -48.67   41
 19  ω     69.00 163.00   1.00    1.00    --   95.80  68.00 -34.11   94
 20  ω     43.00 123.00   1.00    1.00    --   95.80 -82.00 150.00   80
 21  ω    135.00 161.00   1.00    1.00    --   95.80  77.00  60.00   26
 22  ω     96.00 183.00   1.00    1.00    --   95.80  82.00  71.29   87
 23  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 120.00   26
 24  ω    105.00 131.00   1.00    1.00    --   95.80  82.00 120.00   26
 25  ω     50.00 128.00   1.00    1.00    --   95.80 -82.00   0.00   78
 26  ω     65.00  90.00   1.00    1.00    --   95.80  77.00   0.00   25
 27  ω    159.00 185.00   1.00    1.00    --   95.80  77.00   0.00   26
 28  ω     71.00 103.00   1.00    1.00    --   95.80  61.00 -60.00   32
 29  ω    109.00 141.00   1.00    1.00    --   95.80  61.00 -60.00   32
 30  ω     65.00  90.00   1.00    1.00    --   95.80  77.00  30.00   25
 31  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  60.00   26
 32  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 33  ω     63.00  88.00   1.00    1.00    --   95.80  82.00  71.29   25
 34  ω    111.00 180.00   1.00    1.00    --   95.80  57.00   1.93   69
 35  ω     63.00  88.00   1.00    1.00    --   95.80  82.00 -30.00   25
 36  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -90.00   26
 37  ω     51.00 121.00   1.00    1.00    --   95.80 -82.00  90.00   70
 38  ω     12.00  38.00   1.00    1.00    --   95.80 -82.00  90.00   26
 39  ω     72.00  97.00   1.00    1.00    --   95.80  61.00  60.00   25
 40  ω     63.00  89.00   1.00    1.00    --   95.80  82.00-180.00   26
 41  ω    154.00 185.00   1.00    1.00    --   95.80  82.00-180.00   31
 42  ω     63.00  97.00   1.00    1.00    --   95.80  82.00   0.00   34
 43  ω     66.00  92.00   1.00    1.00    --   95.80  74.00 -30.14   26
 44  ω     75.00 109.00   1.00    1.00    --   95.80  45.00-150.00   34
 45  ω    113.00 156.00   1.00    1.00    --   95.80  45.00-150.00   43
 46  ω     63.00  89.00   1.00    1.00    --   95.80  82.00  30.00   26
 47  ω    157.00 182.00   1.00    1.00    --   95.80  82.00  30.00   25
 48  ω     63.00  89.00   1.00    1.00    --   95.80  82.00  90.00   26
 49  ω     45.00 112.00   1.00    1.00    --   95.80 -82.00-150.00   67
 50  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 150.00   26
 51  ω    104.00 185.00   1.00    1.00    --   95.80  77.00  90.00   81
 52  ω     75.00 181.00   1.00    1.00    --   95.80  45.00  30.00  106
 53  ω     66.00  92.00   1.00    1.00    --   95.80  77.00 120.00   26
 54  ω     69.00 128.00   1.00    1.00    --   95.80 -82.00 -90.00   59
 55  ω     67.00  93.00   1.00    1.00    --   95.80  77.00  90.00   26
 56  ω     65.00  93.00   1.00    1.00    --   95.80  77.00-120.00   28
 57  ω     75.00 152.00   1.00    1.00    --   95.80  45.00  60.00   77
 58  ω     72.00  98.00   1.00    1.00    --   95.80  61.00  90.00   26
 59  ω     64.00  90.00   1.00    1.00    --   95.80  82.00-150.00   26
 60  ω     63.00  88.00   1.00    1.00    --   95.80  82.00 -60.00   25
 61  ω    116.00 185.00   1.00    1.00    --   95.80  82.00 -60.00   69
 62  ω     71.00 105.00   1.00    1.00    --   95.80  61.00 -90.00   34
 63  ω     65.00  90.00   1.00    1.00    --   95.80  77.00-150.00   25
 64  ω     65.00 184.00   1.00    1.00    --   95.80  76.00 144.12  119
 65  ω     70.00 178.00   1.00    1.00    --   95.80  63.00 -80.29  108
 66  ω     72.00  97.00   1.00    1.00    --   95.80  57.00   1.93   25
 67  ω     70.00 185.00   1.00    1.00    --   95.80  64.00-146.77  115
 68  ω     94.00 120.00   1.00    1.00    --   95.80 -82.00 -30.00   26
 69  ω     73.00 175.00   1.00    1.00    --   95.80  53.00-174.12  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1152925000
_diffrn_orient_matrix_UB_12      -0.0210151000
_diffrn_orient_matrix_UB_13      -0.0473793000
_diffrn_orient_matrix_UB_21      -0.0725796000
_diffrn_orient_matrix_UB_22      -0.0034372000
_diffrn_orient_matrix_UB_23      -0.0769895000
_diffrn_orient_matrix_UB_31      0.0147690000
_diffrn_orient_matrix_UB_32      0.1473239000
_diffrn_orient_matrix_UB_33      -0.0085826000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1913
_reflns_number_total             1999
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1999
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0517P)²+0.4530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0927
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.46539(4) 0.18432(4) 0.68788(2) 0.05476(17) Uani 1 1 d . . . . .
O1 O 0.56963(12) 0.18203(13) 0.73629(7) 0.0763(4) Uani 1 1 d . . . . .
O2 O 0.39813(14) 0.06715(13) 0.68170(8) 0.0839(4) Uani 1 1 d . . . . .
C1 C 0.58029(10) 0.34232(12) 0.57677(7) 0.0379(3) Uani 1 1 d . . . . .
C2 C 0.50519(11) 0.23351(13) 0.59137(7) 0.0408(3) Uani 1 1 d . . . . .
C3 C 0.46126(13) 0.15991(14) 0.53135(9) 0.0497(3) Uani 1 1 d . . . . .
H3 H 0.412409 0.089831 0.542636 0.060 Uiso 1 1 calc R . . . .
C4 C 0.48925(16) 0.18918(15) 0.45260(9) 0.0567(4) Uani 1 1 d . . . . .
H4 H 0.460298 0.137676 0.411979 0.068 Uiso 1 1 calc R . . . .
C5 C 0.55861(14) 0.29279(16) 0.43606(8) 0.0534(4) Uani 1 1 d . . . . .
H5 H 0.576025 0.312117 0.383759 0.064 Uiso 1 1 calc R . . . .
C6 C 0.60511(11) 0.37216(12) 0.49653(8) 0.0428(3) Uani 1 1 d . . . . .
C7 C 0.67620(13) 0.48077(15) 0.47914(10) 0.0588(4) Uani 1 1 d . . . . .
H7 H 0.691986 0.501408 0.426809 0.071 Uiso 1 1 calc R . . . .
C8 C 0.72194(13) 0.55563(15) 0.53736(13) 0.0677(5) Uani 1 1 d . . . . .
H8 H 0.767620 0.627591 0.524739 0.081 Uiso 1 1 calc R . . . .
C9 C 0.70045(14) 0.52468(15) 0.61625(12) 0.0640(4) Uani 1 1 d . . . . .
H9 H 0.733961 0.575124 0.655809 0.077 Uiso 1 1 calc R . . . .
C10 C 0.63111(12) 0.42168(14) 0.63618(9) 0.0499(3) Uani 1 1 d . . . . .
H10 H 0.617004 0.403275 0.689031 0.060 Uiso 1 1 calc R . . . .
C11 C 0.36956(17) 0.30594(18) 0.72253(11) 0.0725(5) Uani 1 1 d . . . . .
H11A H 0.346361 0.286897 0.775756 0.109 Uiso 1 1 calc GR . . . .
H11B H 0.300086 0.309730 0.689671 0.109 Uiso 1 1 calc GR . . . .
H11C H 0.409915 0.387600 0.721086 0.109 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4306(13) . ?
S1 O2 1.4336(14) . ?
S1 C2 1.7715(13) . ?
S1 C11 1.7584(17) . ?
C1 C2 1.4296(18) . ?
C1 C6 1.4230(17) . ?
C1 C10 1.4201(18) . ?
C2 C3 1.3641(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.405(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.356(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.414(2) . ?
C6 C7 1.411(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.357(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.397(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.364(2) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 117.36(9) . . ?
O1 S1 C2 109.17(7) . . ?
O1 S1 C11 108.76(9) . . ?
O2 S1 C2 108.00(7) . . ?
O2 S1 C11 107.94(9) . . ?
C11 S1 C2 104.91(8) . . ?
C6 C1 C2 116.90(11) . . ?
C10 C1 C2 124.81(12) . . ?
C10 C1 C6 118.28(12) . . ?
C1 C2 S1 122.39(9) . . ?
C3 C2 S1 115.93(11) . . ?
C3 C2 C1 121.67(12) . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.51(14) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.74(13) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.50(13) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 119.65(12) . . ?
C7 C6 C1 118.95(13) . . ?
C7 C6 C5 121.40(13) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.21(15) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.03(14) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.04(15) . . ?
C10 C9 H9 119.5 . . ?
C1 C10 H10 119.8 . . ?
C9 C10 C1 120.45(15) . . ?
C9 C10 H10 119.8 . . ?
S1 C11 H11A 109.5 . . ?
S1 C11 H11B 109.5 . . ?
S1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.774
_oxdiff_exptl_absorpt_empirical_full_min 0.604
